1-[7-Chloro-2-(4-fluorophenyl)pyrazolo[1,5-a]pyridin-3-yl]-2-butyn-1-ol → 1-[7-Chloro-2-(4-fluorophenyl)pyrazolo[1,5-a]pyridin-3-yl]-2-butyn-1-one

HRID 1373793Notes

Reaction equation

HRID 1373793 reaction equation
[Cl:1][C:2]1[N:7]2[N:8]=[C:9]([C:16]3[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=3)[C:10]([CH:11]([OH:15])[C:12]#[C:13][CH3:14])=[C:6]2[CH:5]=[CH:4][CH:3]=1>C(Cl)(Cl)Cl.[O-2].[O-2].[Mn+4]>[Cl:1][C:2]1[N:7]2[N:8]=[C:9]([C:16]3[CH:17]=[CH:18][C:19]([F:22])=[CH:20][CH:21]=3)[C:10]([C:11](=[O:15])[C:12]#[C:13][CH3:14])=[C:6]2[CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 866168551-[7-Chloro-2-(4-fluorophenyl)pyrazolo[1,5-a]pyridin-3-yl]-2-butyn-1-ol

Product 1

HCID 112784021-[7-Chloro-2-(4-fluorophenyl)pyrazolo[1,5-a]pyridin-3-yl]-2-butyn-1-oneYield 92.1%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6212ChloroformSolvent

Procedure

To a solution of 1-[7-chloro-2-(4-fluorophenyl)pyrazolo[1,5-α]pyridin-3-yl]-2-butyn-1-ol (1.04 g, 3.30 mmol) in chloroform (50 mL) was added manganese dioxide (5.70 g, 65.6 mmol). The reaction mixture was stirred at room temperature for 3 hours. The suspension was filtered through a pad of Celite and the filtrate was concentrated in vacuo to give 1-[7-chloro-2-(4-fluorophenyl)pyrazolo[1,5-α]pyridin-3-yl]-2-butyn-1-one (950 mg, 91%). Rf 0.44 (3:1 hexanes:ethyl acetate); 1H NMR (CDCl3) δ 8.49 (d, 1H), 7.73 (m, 2H), 7.50 (t, 1H), 7.19 (m, 3H), 1.71 (3H); 19F NMR (CDCl3) δ −112.58; mp 182–183° C.

Workup

  1. filtrationThe suspension was filtered through a pad of Celite
  2. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-291fff385c2a4dc3b6aec5ee0d94b993
Source dataset
uspto-grants-2007_01
Patent number
US07163940B2

Reaction notes

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